Not What I Was Expecting
by bke.21
Summary: We all know that Cardin is an asshole. But after a blind date, he may end up being a little sore one
1. Chapter 1

**A/N: I dont own RWBY**

 **And now, something completely different. There is a lot of futa stories on here but when Cardin is involved, its always forced. So I thought 'Lets try a futa story with Cardin wanting it.' I may write more on this if i feel like it.**

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I knocked at the door, unsure of what to expect. Living in a big city for the last year, where I didn't really know anybody, had certainly put a crimp in my sex life. Where I used to live, in a much smaller town, during my high school years, I'd been able to get my dick into many tight, warm and willing holes. Unfortunately, all the sexy teen pussy had graduated from high school, and had gone on to college. With the pickings mighty slim, and me not compromising my standards, there was no choice but to head for a bigger city.

Sky, one of the few people that I had gotten to know reasonably well, had set me up on this blind date. Her name was Cinder, he said she was a knock out, a wonderful blend of sexy and dominance. That got my cock eager, if nothing else, at least I'd have a date with a very exotic looking lady.

The door opened, and there she was, smiling at me. Oh my god, Cinder looked as good as Sky had told me. Jet black hair, parted on the left, and hanging down to just below her shoulder blades. Her face was a knock out, her Asian and Europian features in a wonderful blend of sexiness, with molten gold eyes. Being that I am 6 feet, I lust after tall women, and with Cinder being 5 feet 11 inches, oh yeah, perfect. Her chest was small, proportionate to her height, and I was relieved to see no hint of artificial enlargement. I CANNOT stand fake tits, if a woman isn't secure enough to be happy with the melons that Mother Nature endowed her with, that is a deal breaker.

"Cardin, hello, welcome, please come in" Cinder said, with a definite English accent.

I did as she asked, watching as she turned to lead me. Oh yeah, what a knockout, Cinder was wearing a black, loose flowing dress, that hid her charms somewhat, but just made me the more eager to uncover those naked charms and assets. She was wearing black stockings, I hoped it wasn't pantyhose, so unsexy. The world lost a good deal of female sexiness when pantyhose replaced stockings and garter belts.

In her living room, Cinder gave me a martini, and we clinked glasses. The martini was smooth, and I quickly downed it, and she was happy to refill my glass.

She surprised me when she suddenly asked, "Cardin, what do you expect from our date, what are you hoping for?"

I was nonplussed by such a direct question, and I tried to collect my thoughts.

She said, "Perhaps it would be better if I told you what I want. I want something different, I'm not interested in some plain, vanilla sex, if that is all you are hoping for, well, we can say goodnight right now. If, however, you are willing to try something very different, we could have a wonderful time."

With her body, her voice and her face, I'd try to swim the English Channel, and I eagerly agreed. She smiled, and led me upstairs, in her bedroom, she slowly stripped me down, planting soft, delicate kisses, bringing my prick up to a ready, stiff 7 inches.

"Lay down Cardin."

She smiled, reached up to her neck, and started to undo the collar holding her dress together. As the dress fell away, I got a look at her melons, nice, orange sized, with stiff, excited nipples. She was indeed wearing stockings, with a black garter belt. I gazed towards the triangle of her sex, it seemed something was blocking my view. I was confused, then realized that she was sporting a hard, stiff 7 inches! Holy Shit!

"Yes Cardin, it is a real penis. I was born with both male and female organs, though I am more outwardly female, my cock is more than just an appendage, it gets as excited and as ready as yours does. My parents thought that since nature made me this way, why subject me to surgery, to correct it to some societal norm? I was brought up with a good sense of self worth, of course, my difference was kept concealed from a world that would be quick to make a harsh judgement. In my teens, when my cock started to develop, my panties had a pouch at the front, that I could tuck my cock into, then make sure it was pulled up tight against me. If you are still up for something different, I'd like to take your asshole. Are you still an asshole virgin, Cardin?" she cooed.

Wow, what a date. I was still an asshole virgin, and never thought I'd end it. I had been having darkly exciting thoughts, about having a girlfriend strap on a dildo, and bust my back door cherry, but working up the nerve to actually ask that? And here was an absolute knock out, female enough for me, who wanted to break me open with a real cock. I nodded, eager for her to take me up the ass.

She smiled, and told me to turn over. On my hands and knees, I felt her pull my cheeks apart, then the electrifying sensation as she applied her hot, wet tongue to my asshole. I growled with pleasure, the feel of her tongue teasing and running over the tight rim was nothing short of mind blowing. She brought a finger into play, and I could feel it push in to the first knuckle. I worked on relaxing the tight muscle ring, as she continued to lick and finger my asshole for a good long time. I could feel myself starting to relax more.

"Turn over Cardin, I slipped a valium into your drink, just something to relax you and make your virgin breaking a little easier," she whispered.

"Yeah, I'm ready for it Cinder" I whispered.

She smiled as slid a large pillow under my hips. I was lifted up, with my ass free of any obstruction, and I felt well greased fingers sliding slippery lube over my tight rim, then a finger worming its way in, spreading it around the tight walls. Cinder slid a coating of lube up her stiff cock, the lube making her erection gleam in the dim light.

"Grab behind your knees, and pull them towards your chest."

I did so, feeling my asshole spread apart slightly, ready for her cock. She got into position, her legs straddling the pillow, pushing another, smaller pillow under my ass to raise it up for the right level, setting my ass up for fucking. I could feel her lubed up cock head pressing against me.

"Now, just relax baby, you'll love it" Cinder whispered huskily, "I'll bust your cherry gently."

I felt the push, then the lubed head slipped in. I hissed a bit, she held it steady, and urged me to relax. I worked on it, and told her to go on. Inch, by inch, slowly, slowly, she pushed into me, my tight ass walls getting their very first fuck. The pain was noticeable, but not unbearable, and I was grateful for the valium she had slipped into my drink. She stopped with about an inch left.

"Ok baby, one last push, and your virgin busting will be complete, are you ready baby?" she cooed.

"Yeah, I'm ready, complete my cherry busting!"

Cinder thrust her hips forward, and I felt my ass get the stretch as she buried the last inch, going in right to the balls. I let out a moan as I felt it, it was actually feeling pretty good, the pain of my asshole cherry being busted was mixing with a pleasurable pulsing, and as she paused, I urged her on.

"Yeah, oh yeah, keep fucking me, I want my asshole to get fucked good. Give it to me Cinder!"

She smiled down at me, and leaning forward, my legs went over her shoulders, and she started a slow, steady rhythm. I pulled my hands down and curled them around the sexy cheeks of her ass, pulling her against me, letting me know that I was starting to enjoy it more and more. The relaxation of the valium, and my tight asshole giving up the clench, adjusting to the plunges of her cock, let me enjoy it. The fact that I was being taken just like a vanilla female, and the stroking of her throbbing cock over my prostate was turning my cock into a red hot poker, it was harder than ever. Cinder grinned as she saw my eager hardness, she grasped it, and started to stroke my cock. I growled with pure pleasure, oh, her hands knew what they were doing, she stroked me in time to the plunges of her cock up my ass, and Cinder started to make noises of pleasure, her growls and gasps of joy letting me know that she was closing in on her climax.

Cinder grunted, "Are you ready to cum baby?"

"Yeah, oh fuck yeah" I groaned as my orgasm rose.

My cock swelled up tight, just as Cinder let out a drawn out shriek, and I felt her cock pulsing wildly as she went off, over and over, and the feel of her cum gushing, filling my ass with her heated load, drove me over the edge. I growled as my cock erupted, three large ropes shot out, splattering against my chest, my cock continued erupting over Cinder's milking hand, a geyser of hot, white cum spilling down over her curled fist and onto my belly. I was thrusting and grunting, spilling even more cum as it slid down the length of my shaft. My ears were ringing and my breath was coming so fast I could barely control it.

When I got my bearings back, Cinder was smiling at me, and she slowly withdrew her cock from my ass. She started to lick up the cum that was splattered over me, eager to get every drop. She flopped down next to me, and grinned.

"I must make sure that your yummy load is not wasted on a towel, not when my mouth is so eager to swallow it all", she purred, "Cardin, would you like to join me in the shower?"

Soon we were under the hot spray of water, soaping up, and it was a surreal experience to be in the shower with such a gorgeous lady, watching as she soaped up her hands, and carefully washed her cock, wild. As I soaped up her gorgeous curves, she sighed with pleasure.

She said, "So Cardin, did you like it?"

"Oh yeah, I fucking loved it!" I enthused.

"Excellent, I want you to do me now. I do have a vagina, if you'd like, but I love getting my ass fucked, would you like to fill my tight ass Cardin?" Cinder cooed.

Just the thought of taking this gorgeous creature's ass drove me up to rock hardness, and Cinder smiled at the rise.

"I take it that means Yes", she purred, "Let's get dry, then take me back to bed, and let me have it."

Back in the bedroom, I put her on hands and knees, and got my tongue down to her asshole, running over the tight twitchy rim, again and again.

"Fuck, oh fuck I love it, lick and finger my asshole lots, then fuck my tight hole, I'm gonna love it!" Cinder growled huskily.

I brought my fingers into play, and licking that tight hole, and running my fingers into her, feeling the tight grip and listening to her moans of pleasure, kept my cock granite hard, so ready to return the fucking. She rolled over, lifted her legs up, and placed herself in the exact same position.

"I want to get it the exact same way, take my ass the same way I took yours, let me have it Cardin, I want your cock up my tight hole!"

I lubed up, and placing it at the entrance, started a slow and steady push.

"Yes, yes, fill my hot, tight hole, I love it, drive it in Cardin, bury it NOW!"

I did as she wanted, letting out a growl of pleasure. Cinder's asshole was the tightest, hottest hole I have ever had the pleasure of driving my cock into. The heat and the tight clamp of her smooth ass walls surrounded me as I buried my cock in one bold thrust. Cinder let out a drawn out cry of pleasure as I went in right to the balls.

"Yes, yes, oh yes, just what I needed, now give it to me Cardin, fuck my ass, really ride me, and flood my tight hole with a thick, juicy load!"

I had her ankles up by my shoulders, her ass spread around my cock, and I gave her what she needed. I plunged in, over and over, my cock buzzing from the hottest, tightest grip I had ever had. Her cock was back up to rock hardness, and I quickly wrapped my hand around it, eager to stroke her to a shattering climax. She started to grunt and moan as my hand stroked up and down her prick, in time with the driving fuck of my cock surging up her ass.

"Fuck, yeah, fuck my ass, fuck me fuck me!"

My cock was ready to blow, I felt the jerk and the swell of my cock head, Cinder let out a cry of pleasure as her ass hole was stretched to the max around my cock, and I felt the cum surging up. With a wild groan of pure pleasure, my cock erupted, I could feel my cock pulsing and pumping a fresh volley of cum, filling up Cinder's tight ass. The feel of my cum pouring hotly into her set Cinder off.

"Fuck, fuck, fuck, fill my ass, yes, yes, yes, YEEEESSSSS!"

Her drawn out howl of pleasure filled the bedroom, her cock pulsing in my hands as she erupted. Two shots of thick cum flew up, splattering just below her breasts, the rest flowed out like a fountain of hot, white spunk, spilling down the length of her shaft, over my curled fist and onto her belly. I stroked her until her cock was dry, then, with her seeing what I was doing, I quickly brought my hand up, and licked off all the cum. Her eyes glowed with pleasure, as I slid out of her well ridden asshole, and quickly got my mouth busy, licking up thick, gooey trails of her cum, relishing the taste. She had done it for me, so it was only fair that I clean up her incredible body, too.

I took a quick side trip into the bathroom, washed off my cock, marveling at my good fortune. A blind date, who would have ever thought I'd discover such a diamond in the rough?

This may have been our first date, but it was not going to be our last, the sight of her in bed, stretched out, inviting me between the sheets, would bring me back eagerly.


	2. A night out

Knocking on the door, I was almost trembling with anticipation. This was going to be my second date with Cinder, I was wearing my best suit, I wanted to take her out, have a nice dinner, squire her around and show her off, she was unlike any woman I had ever dated, and I wasn't referring to her anatomical differences.

The door opened, and there she was, my god, looking just a hot and desirable as when I first set eyes on her. She was dressed casually in a T shirt and tight jeans that showed off her bulge, I could see why she had to wear dresses in public.

Her blue eyes sparkled, and she cooed, "I wore these jeans just for you, come in Cardin, and come upstairs with me while I change."

Walking behind her, I could see the sexy heart shape of her ass, snugged in the tight rear of her jeans, it made me remember the feel of powering my hard cock right between those sexy cheeks, and I could feel my cock respond.

In her bedroom, she stripped, flashing me a sultry smile as I took in her naked charms, her cock rising up, as hard and eager as mine.

"I will go crazy if I don't get some release before we go out," she purred, "Come over here Cardin, get yourself naked."

I did as she asked, and she had me stand right in front of her, our cocks almost touching.

"Now, stroke my cock baby, I'll stroke yours, I want to feel you shooting your load all over my cock, while I fire my load all over yours!"

I grasped her stiff erection, while I felt her hand grasp mine. We started to stroke each other in unison, Cinder has a wonderful touch, I could feel my cock get even harder, and I felt Cinder's cock start to throb, twitching and surging in my hand.

"Yeah oh yeah, I love the way you stroke my cock baby, I can't wait for us to splatter our loads" Cinder cooed.

I could feel my balls start to churn, our breathing started to become choppy, we were both letting out grunts and sighs of pleasure, fucking each others cock with our hands. I could feel the tremors of excitement start running through Cinder's cock, matching the twitching of lust shooting through mine.

Cinder howled, grunted, her cock swelled up tight, and erupted. A geyser of hot, white cum splattered against my stomach, my hand milked her, and she gushed several thick ropes of cum all over my cock, and her hand. The feel of her hot load splattering against my cock was electric, and it immediately sent me over, and I was cumming, too, her hand fucking my cock expertly, firing a thick rope against her stomach, and more thick ropes flying all over her cock, feeling the splatter of my cum gushing over her cock and my stroking hand. We expertly milked each other, both of us grunting with pleasure and spilling every drop as our loads slid down the length of each others cock.

Her eyes bright, she released me, gave me her hand as she took my hand, I got the message, and we licked off the spunk that we had splattered over each others hands as we came, then she urged me on, and we used our fingers to scoop up the thick, juicy spray that we had splattered over each other. Her face glowed with pleasure, and she gave me a smile that made my heart melt.

"Oh yes, so good, just what I needed" Cinder whispered, "Cardin, as you can probably figure out, being transgendered makes a healthy sex life very difficult, it's bad enough with the offhand comments people make, let alone meeting someone I'd really like to get to know better, and even hinting that I was somehow different shutting it down quickly. Yeah, sure, I can masturbate, but damn, I need the real thing, fantasy is fine to a point. Now I'm into an overdrive state, I'll be more than eager when we get home again. I want to make up for lost time! Think you'd like to help me make up that lost time?" she cooed, a teasing note in her voice.

"Oh yeah baby, you are the sexiest lady I've ever had the pleasure of dating. When you want it, I'll be ready for it!"

Her eyes glowed as she smiled at me. As I got dressed, she showed me her special panties, pulling them on, she carefully fit her cock and balls into the front pouch, which had a velcro at the top of the pouch, which attached to a small strip of velcro at the top of her panties.

"Made special for me by a very understanding group of people, like me, so we can keep our secret," she said, with a sly smile. "Big enough for my cock to grow hard, and with the velcro fastener, keeping it securely against my body. Now, you go and wait in the living room, help yourself to a drink, could you make me a martini? I'll be there in two shakes of a lamb's tail."

I retreated to the living room, smiling all the way. I got the gin and vermouth, and whipped up two dry martinis. Popping an olive in each, standing by the bar, I could hear the soft tread of her coming downstairs. I turned to look, and oh my god, what a vision. She was wearing a fire engine red dress, that was fastened at her right shoulder, covering it, then the dress slanted obliquely across her body, dipping below her left shoulder, leaving it bare. It fit snugly around her, she was going braless, and I could see her orange sized breasts pressed against her top, the stiff, perky nipples making their presence known, the dress hugged her waist, then the skirt billowed out, floating around her just above knee level. She was also wearing jet black stockings, and I could feel myself getting revved up again. She grinned at me, gave me a fashion model turn.

"You like, sweetheart?" she purred.

"Yeah, I like very much" I growled, huskily.

Crossing the distance, I grabbed her, and our lips were quickly locked together, lips pressed urgently, tongues dueling madly in passion filled swirls. Her hand reached down, as I slipped my hands under her skirt, and as her fingers stroked and caressed my bulge, my hand found her pouch, and I stroked at the outline of her hard, straining cock, nestled securely in her pantie pouch. We broke the kiss, and Cinder smiled at me.

"If I wasn't so hungry, I'd drag you upstairs" I said huskily, "But I want to take you out, squire you around, show you off. The way you look baby, everyone will be looking, envious as hell that I have such a vision of loveliness on my arm."

Her smile became radiant, and she led me over to the bar. Clinking our glasses, we sipped at our drinks.

On the street, we hailed a cab, and in a few minutes, we were at the best steak house in town, The RCM club. We walked in, fortunately we had a reservation, as it was impossible to be seated just as a walk-in. As the maître led us to our table, I could see every male head turning, watching Cinder pass by, leaving their dates fuming as they couldn't take their eyes off her. I smiled inwardly, yes indeed, I could understand the lust filled looks directed her way, and reveled in the knowledge that I would be the lucky one to share her naked charms and assets. I wondered, idly, if their desire would be so hot once they got a total look at her when she was stripped down and ready for action. I smiled again, I was going to tbe the lucky one to enjoy that vision, and I would take full advantage of her desire for me.

After a sumptuous dinner, we went to Maroni's, a dance club just down the street, that liked to play a well balanced mix of danceable tunes, from slow crooners like Dean Martin and Frank Sinatra, to the latest hot dance tunes. On the floor, Cinder showed how well she could shake her ass, she had my cock ready and eager, and judging by the hungry looks from the tables closest to us, I wasn't the only one.

The DJ swung into a medley of slow dance tunes from the 40's and 50's, and Cinder eagerly stepped into my arms, her head on my shoulder, her body pressed close to mine as we moved to the music.

She whispered in my ear, "So wonderful, I feel so wonderful."

I felt her bulge, pressed tightly against me, filling her secret pouch, and I kept her tight against me, so she could feel my cock pressing urgently, letting her know that I was as warmed up as she was.

When the set had ended, those wonderful blue eyes gazed into mine, and she cooed, "Take me home Cardin, I can't wait another minute, I need you, and I want you now!"

In her bedroom, our clothes flew off, Cinder smiled as her panties came off, her cock grown to full, impatient need.

"Doggy style, do me from behind sweetheart, and this time, give my pussy a filling, drive it in, and fill me with a thick load."

My cock was aching for it, seeing her on hands and knees, in garter belt and stockings, made me granite hard. I plastered my mouth against her, licking at the juices that were slicking up her tight lips.

"Yes, oh yes you sweetheart, lick up my juices."

Her tight lips were almost gushing, I quickly raised up, pressing my cock against her, I slid in. Our growls of mixed pleasure filled the room, her pussy felt like liquid fire, surrounding my cock in a burning, tight grip, as I drove in right to the balls. I reached around her body, grasped her cock, and started to stroke her straining cock as I drove into her, stroking back and forth as her hips rocked back to meet each stroke.

"Yes, oh yes you sweet, sweet man, ride me Cardin, fuck me hard, and blow that thick load!"

My cock was too excited, and when I felt a hand reach under and grasp my balls, and start squeezing, I reached my peak, it brought on the explosion and my jetting cock filled her, throbbing and jerking, pumping a flood of hot spunk deep inside her.

I quickly pulled out and arranged myself, I knew what was coming, and I wanted it.

"Give it to me Cinder, take my ass and fuck me good."

"Yes, you sweet, sweet man, I will give your ass a loving ride, baby."

I felt her mouth descend, and her tongue and fingers went to work, licking at the tight rim of my ass, those electric tingles of burning pleasure filled me again, the sensation shooting through me, bringing a growl of pleasure. Her finger slipped in, sliding around the smooth inner wall, I worked on relaxing, and I could feel it loosen up.

"Oh, you must be very ready!" Cinder giggled, as she felt the loosening.

I felt Cinder swing into position, her hands grasped my hips, pulling me up into the best position, I felt the head against me, and the press as her well lubed cock slid in smoothly. I grunted with pleasure, the feel of my tight ass walls getting the stretch felt so good. She slid it in, smoothly and slowly, I felt a small twinge of pain, but it did nothing to lessen the pleasure I was feeling.

"Yeah, oh yeah baby, feels so good, fuck my ass, I want your load right up my tight hole!"

Encouraged, Cinder proceeded to give me exactly what I wanted, her hard stiff cock sliding into me, fucking my ass, sending sizzling bolts of pleasure racing through me. Cinder was letting out grunts of lust and pleasure, as my asshole got the reaming I needed.

"Yes, oh fuck yes, your ass is so tight, I'm gonna blow my load baby, gonna fill up your tight hole!" Cinder growled.

"Yes, fuck yeah, let it go, flood me baby, fill me up!" I growled back.

Letting out a drawn out howl of pleasure, Cinder's throbbing cock erupted, I could feel the explosion, and the jetting streams of spunk flooding my tight back door.


End file.
